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Cheap flights from Alabama to Chicago from $68

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Alabama to Chicago departing on 7/31. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Alabama to Chicago

Cheap round-trip flights

Enter your travel dates to find the best prices.
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$82Allegiant Air
Mon, Aug 3 - Mon, Aug 17
Allegiant Air Logo
6:10 pm - 8:30 pm
VPS
-
MDW
2h 20mnonstop
Allegiant Air Logo
9:25 pm - 11:39 pm
MDW
-
VPS
2h 14mnonstop
$88Allegiant Air
Mon, Aug 3 - Mon, Aug 17
Allegiant Air Logo
6:07 pm - 8:25 pm
VPS
-
MDW
2h 18mnonstop
Allegiant Air Logo
6:44 pm - 8:55 pm
MDW
-
VPS
2h 11mnonstop
$101Allegiant Air
Fri, Oct 23 - Mon, Oct 26
Frontier Logo
9:59 am - 10:58 am
ATL
-
MDW
1h 59mnonstop
Frontier Logo
7:25 am - 10:23 am
MDW
-
ATL
1h 58mnonstop
$148Frontier
Sun, Sep 27 - Tue, Sep 29
Frontier Logo
8:59 pm - 10:03 pm
ATL
-
MDW
2h 04mnonstop
Frontier Logo
12:11 pm - 3:13 pm
MDW
-
ATL
2h 02mnonstop
$151Frontier
Wed, Jul 22 - Sat, Jul 25
Multiple Airlines Logo
12:00 pm - 9:58 pm
VPS
-
MDW
33h 58m
2 stops
Multiple Airlines Logo
6:44 pm - 8:55 pm
MDW
-
VPS
2h 11mnonstop
$257Multiple Airlines
Fri, Oct 23 - Mon, Oct 26
Delta Logo
3:04 pm - 6:33 pm
CHA
-
MDW
4h 29m
1 stop
Delta Logo
9:24 am - 2:17 pm
MDW
-
CHA
3h 53m
1 stop
$269Delta
Tue, Aug 4 - Tue, Aug 11
Southwest Logo
5:00 am - 6:50 am
BHM
-
MDW
1h 50mnonstop
Southwest Logo
8:45 pm - 10:35 pm
MDW
-
BHM
1h 50mnonstop
$273Southwest
Sat, Aug 1 - Sat, Aug 1
Southwest Logo
4:55 pm - 8:10 pm
BHM
-
MDW
3h 15m
1 stop
Southwest Logo
10:05 am - 11:45 am
MDW
-
BHM
1h 40mnonstop
$283Southwest
Wed, Aug 26 - Sat, Aug 29
Delta Logo
7:20 pm - 10:15 pm
CHA
-
MDW
3h 55m
1 stop
Delta Logo
6:00 am - 12:22 pm
MDW
-
CHA
5h 22m
1 stop
$284Delta
Wed, Jul 15 - Wed, Jul 22

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Allegiant Air flights from Alabama to Chicago Midway Airport

Our best Allegiant Air deals on Alabama to Chicago Midway Airport flight tickets
Allegiant Air
Aug 3
VPS6:10 pmValparaiso Destin-Ft Walton Beach
2h 20m
MDW8:30 pmChicago Midway
Aug 17
MDW9:25 pmChicago Midway
2h 14m
VPS11:39 pmValparaiso Destin-Ft Walton Beach
$82
Allegiant Air
Aug 3
VPS6:10 pmValparaiso Destin-Ft Walton Beach
2h 20m
MDW8:30 pmChicago Midway
Aug 17
MDW9:25 pmChicago Midway
2h 14m
VPS11:39 pmValparaiso Destin-Ft Walton Beach
$88
Allegiant Air
Oct 23
VPS6:07 pmValparaiso Destin-Ft Walton Beach
2h 18m
MDW8:25 pmChicago Midway
Oct 26
MDW6:44 pmChicago Midway
2h 11m
VPS8:55 pmValparaiso Destin-Ft Walton Beach
$101

Frontier flights from Alabama to Chicago Midway Airport

Our best Frontier deals on Alabama to Chicago Midway Airport flight tickets
Frontier
Sep 27
ATL9:59 amAtlanta Hartsfield-Jackson
1h 59m
MDW10:58 amChicago Midway
Sep 29
MDW7:25 amChicago Midway
1h 58m
ATL10:23 amAtlanta Hartsfield-Jackson
$148
Frontier
Jul 22
ATL8:59 pmAtlanta Hartsfield-Jackson
2h 04m
MDW10:03 pmChicago Midway
Jul 25
MDW12:11 pmChicago Midway
2h 02m
ATL3:13 pmAtlanta Hartsfield-Jackson
$151
Frontier
Oct 14
ATL9:59 amAtlanta Hartsfield-Jackson
1h 59m
MDW10:58 amChicago Midway
Oct 18
MDW6:40 amChicago Midway
2h 05m
ATL9:45 amAtlanta Hartsfield-Jackson
$153

momondo Fare Finder

 
Customize your flight search to find flights from Alabama to Chicago Midway Airport that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, momondo users made 832,500 searches. Data last updated July 4, 2026.
Use the filters below to find and compare flights from Alabama to Chicago Midway Airport that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 8/3

6:10 pm-8:30 pm

Nonstop2h 20m

Chicago Midway

Mon 8/17

9:25 pm-11:39 pm

Nonstop2h 14m

$82

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Mon 8/3

6:10 pm-8:30 pm

Nonstop2h 20m

Chicago Midway

Mon 8/17

9:25 pm-11:39 pm

Nonstop2h 14m

$88

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 10/23

6:07 pm-8:25 pm

Nonstop2h 18m

Chicago Midway

Mon 10/26

6:44 pm-8:55 pm

Nonstop2h 11m

$101

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Sun 9/27

9:59 am-10:58 am

Nonstop1h 59m

Chicago Midway

Tue 9/29

7:25 am-10:23 am

Nonstop1h 58m

$148

AtlantaChicago

ATL - MDW

ATLMDW

Atlanta Hartsfield-Jackson

Wed 7/22

8:59 pm-10:03 pm

Nonstop2h 04m

Chicago Midway

Sat 7/25

12:11 pm-3:13 pm

Nonstop2h 02m

$151

ValparaisoChicago

VPS - MDW

VPSMDW

Valparaiso Destin-Ft Walton Beach

Fri 10/23

12:00 pm-9:58 pm

2 stops33h 58m

Chicago Midway

Mon 10/26

6:44 pm-8:55 pm

Nonstop2h 11m

$257

ChattanoogaChicago

CHA - MDW

CHAMDW

Chattanooga Lovell Field

Tue 8/4

3:04 pm-6:33 pm

1 stop4h 29m

Chicago Midway

Tue 8/11

9:24 am-2:17 pm

1 stop3h 53m

$269
Quickest round-trip

BirminghamChicago

BHM - MDW

BHMMDW

Birmingham

Sat 8/1

5:00 am-6:50 am

Nonstop1h 50m

Chicago Midway

Sat 8/1

8:45 pm-10:35 pm

Nonstop1h 50m

$273

BirminghamChicago

BHM - MDW

BHMMDW

Birmingham

Wed 8/26

4:55 pm-8:10 pm

1 stop3h 15m

Chicago Midway

Sat 8/29

10:05 am-11:45 am

Nonstop1h 40m

$283

ChattanoogaChicago

CHA - MDW

CHAMDW

Chattanooga Lovell Field

Wed 7/15

7:20 pm-10:15 pm

1 stop3h 55m

Chicago Midway

Wed 7/22

6:00 am-12:22 pm

1 stop5h 22m

$284

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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See travel insights to Chicago from

How to get the cheapest flight ticket from Alabama to Chicago Midway Airport

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

What is the cheapest month to fly to Chicago Midway Airport?

The month of May is, on average, the cheapest month to fly to Chicago Midway Airport from Alabama, with most prices found around $0. If you are unable to visit Chicago Midway Airport during the month of May, then departing from Alabama during the month November is also very affordable. Most momondo users find prices during this month for around $199.

What is the cheapest day to depart on your flight to Chicago Midway Airport?

According to our data, Wednesday is the cheapest day to fly to Chicago Midway Airport from Alabama. The lowest ticket price found for a Wednesday departure recently was $397. Keep in mind that prices can always vary depending on your route and whether or not you are flying domestic or international. On the other hand, Sunday is the most expensive day to depart from Alabama because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $496.

What is the cheapest time of day to depart on your flight to Chicago Midway Airport?

Flying to Chicago Midway Airport from Alabama in the morning is the least expensive time of day to depart. momondo users have found prices as low as $416 when looking at flights departing in the morning. Try not to purchase tickets at noon because they tend to be around $452. Of course, these prices can vary depending on the time of year and what airport you fly to.

What is the cheapest Alabama to Chicago Midway flight route?

Fly from Birmingham to Chicago Midway for the best Alabama - Chicago Midway flight prices

What cabin class options are available on Alabama to Chicago Midway Airport flights?

There is only 1 cabin class available to choose from on Alabama to Chicago Midway Airport flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

Can stopping save me money on Alabama to Chicago Midway Airport flights?

You could potentially save up to 30% on your flight if you consider stops on a Alabama to Chicago Midway Airport flight.

Cheap Alabama to Chicago Midway Airport flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Alabama to Chicago Midway Airport

Best Price Found

$211

Fastest flight time

1h 45m

Direct flights

Every day
The best one-way flight to Chicago Midway Airport from Alabama in the past 72 hours is $211. The best round-trip flight deal from Alabama to Chicago Midway Airport found on momondo in the last 72 hours is $406.
The fastest flight from Alabama to Chicago Midway Airport takes 1h 45m
Direct flights go from Alabama to Chicago Midway Airport every day.
Search flight deals

Frequently asked questions about flying from Alabama to Chicago Midway Airport

  • When did momondo last update prices for flights from Alabama to Chicago Midway Airport?

    Prices for flights from Alabama to Chicago Midway Airport are refreshed on a daily basis.

  • How many operators does momondo search for flights from Alabama to Chicago Midway Airport?

  • How old do you have to be to fly from Alabama to Chicago Midway Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Alabama to Chicago Midway Airport.

  • What documentation or ID do you need to fly to Chicago Midway Airport?

    The travel and health documents required for your trip to Chicago Midway Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Chicago Midway Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

  • What is the most popular plane model from Alabama to Chicago Midway Airport?

Best airlines flying from Alabama to Chicago Midway Airport

Compare and see reviews for airlines that fly from Alabama to Chicago Midway Airport with momondo
Airline
Rating
Free Cancellation
Price
SouthwestPriceFrom $260Free CancellationRating
7.9
4,250 reviews
Search Southwest flights
DeltaPriceFrom $268Free CancellationRating
7.8
8,454 reviews
Search Delta flights

Traveling to a place near Chicago?

Book flights to Chicago if you plan to visit one of these locations
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New Buffalo
Hammond
Portage
Benton Harbor
Saint Joseph
Lansing
Valparaiso
Schererville
Munster
Crown Point
Monticello
Chesterton
Porter
Griffith
Saint John

Why use momondo?

Why should I use momondo to find a flight deal from Alabama to Chicago?

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Alabama to Chicago. Millions of users trust and use momondo every year so you are in good hands.

Can I find flights from Alabama to Chicago with flexible booking policies on momondo?

Flights from Alabama to Chicago with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Alabama to Chicago?

momondo provides multiple filters to help you find the best flight to Chicago from Alabama. Filter by price, airline, airports, cabin, aircraft, payment method, number of stops and more.

I’m not ready to book a flight from Alabama to Chicago right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Alabama to Chicago flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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